BOC-D-TIC-OH Chemical Properties

Melting point:

122-123℃

Boiling point:

420.18°C (rough estimate)

Density 

1.1311 (rough estimate)

refractive index 

1.5080 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.88±0.20(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

115962-35-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29334900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

BOC-D-TIC-OH Usage And Synthesis

Uses

BOC-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid can be used as an organic synthesis intermediate. It can be obtained by protecting (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride with Boc, or by reacting L-Phe with aqueous formaldehyde solution and tert-butoxyanhydride.

Chemical Properties

white to light beige powder

Synthesis

The general procedure for the synthesis of (R)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid from di-tert-butyl dicarbonate and (S)-(-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was as follows: (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (50.0 g, 282 mmol) was suspended in 1,4-dioxane ( 1000 mL) and water (500 mL) in a solvent mixture with vigorous stirring. Subsequently, sodium bicarbonate (47.4 g, 564 mmol) and di-tert-butyl dicarbonate (67.7 g, 310 mmol) were added and the reaction mixture was stirred continuously at room temperature for 6 days. After completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent. The concentrated residue was dissolved in water (2000 mL) and acidified by adding 30% w/v aqueous sodium bisulfate monohydrate (300 mL). The acidified aqueous phase was extracted with chloroform (3 x 1000 mL) and the organic phases were combined. The organic phases were sequentially washed with saturated saline, dried over anhydrous sodium sulfate, and subsequently concentrated under reduced pressure to afford the target product (R)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (90.0 g, quantitative yield) as a thick slurry. The product was confirmed by LCMS analysis: retention time (RT) 3.64 min; mass spectral data: m/z 178.1 [M-Boc + 2H]+; m/z 276.1 [M-H]-.

References

[1] Patent: WO2017/153513, 2017, A1. Location in patent: Page/Page column 78
[2] Patent: WO2017/153515, 2017, A1. Location in patent: Page/Page column 62
[3] Patent: WO2017/153520, 2017, A1. Location in patent: Page/Page column 44; 47
[4] Patent: WO2017/153519, 2017, A1. Location in patent: Page/Page column 56; 59
[5] Tetrahedron Letters, 2001, vol. 42, # 43, p. 7559 - 7561

BOC-D-TIC-OH(115962-35-1)Related Product Information

• H-TIC-OH
• D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
• BOC-L-TIC-OH
• BOC-D-TIC(OH)-OH,Boc-D-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Boc-7-hydroxy-D-Tic-OH Boc-D-Tic(OH)-OH)
• BOC-HYDROXY-TIC-OH,BOC-L-TIC(OH)-OH
• BOC-D-TIC-OH