N-(TERT-BUTOXYCARBONYL)-D-PROLINAL Chemical Properties

Boiling point:

228 °C(lit.)

alpha 

+83°(23℃, neat)

Density 

1.059 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.461(lit.)

Flash point:

>230 °F

storage temp. 

-20°C

form 

Liquid

pka

-3.03±0.40(Predicted)

Specific Gravity

1.059

color 

Colorless to yellow

optical activity

[α]23/D +83°, neat

Sensitive 

Air Sensitive

InChI

InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h7-8H,4-6H2,1-3H3/t8-/m1/s1

InChIKey

YDBPZCVWPFMBDH-MRVPVSSYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC[C@@H]1C=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29339980

MSDS

• Language:English Provider:SigmaAldrich

N-(TERT-BUTOXYCARBONYL)-D-PROLINAL Usage And Synthesis

Chemical Properties

Clear colorless to yellow liquid

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

1. tert-Butyl (2R)-2-formylpyrrolidine-1-carboxylate (15.9 g, 37.4 mmol) was added in batches to a stirring solution of tert-Butyl (2R)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (5.0 g, 24.9 mmol) in dichloromethane (75 mL) under nitrogen protection over a 5-minute dosing period. 2. The reaction mixture was stirred for 1 hr. to form a suspension.3. The suspension was filtered through a diatomaceous earth pad and the filter cake was washed with dichloromethane (100 mL).4. The filtrate was concentrated under pressure to give the crude product.5. The crude product was purified by neutral silica gel column chromatography to give BOC-D-prolinyl aldehyde (4.4 g, 89% yield) using 12% ethyl acetate/hexanes as eluent.

References

[1] Patent: WO2015/120390, 2015, A1. Location in patent: Page/Page column 97; 178
[2] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
[3] Patent: WO2015/118342, 2015, A1. Location in patent: Page/Page column 94; 95
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 12, p. 3190 - 3198
[5] Tetrahedron Letters, 1990, vol. 31, # 28, p. 3957 - 3960

N-(TERT-BUTOXYCARBONYL)-D-PROLINAL(73365-02-3)Related Product Information

• N-(TERT-BUTOXYCARBONYL)-L-PROLINAL,(S)-N-Boc-pyrrolidine-2-carboxaldehyde, N-(tert-Butoxycarbonyl)-L-prolinal
• (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid
• BOC-D-PRO-OSU
• D-1-N-Boc-prolinamide
• N-(TERT-BUTOXYCARBONYL)-D-PROLINAL
• (3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid
• BOC-D-PRO-OME
• (2R,4R)-1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
• BOC-D-PRO-D-PHE-OH
• (R)-2-(2-ETHOXYCARBONYL-ACETYL)-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• BOC-D-PRO-GLY-OH
• BOC-D-PRO-PAM RESIN
• (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• BOC-CIS-3-HYDROXY-D-PROLINE
• BOC-D-PRO-PHE-OH
• (2R,5S)-BOC-5-PHENYL-PYRROLIDINE-2-CARBOXYLIC ACID
• BOC-(S)-ALPHA-BENZYL-PROLINE
• AKOS 92832