(3-HYDROXYMETHYL-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

51 °C

Boiling point:

0°C

Density 

1.106±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

2-8°C

pka

12.16±0.46(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C13H19NO3/c1-13(2,3)17-12(16)14-8-10-5-4-6-11(7-10)9-15/h4-7,15H,8-9H2,1-3H3,(H,14,16)

InChIKey

QNDFFICIIGQGDV-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCC1=CC=CC(CO)=C1

CAS DataBase Reference

226070-69-5

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/22-36/37/38-22

Safety Statements 

22-26-36/37/39

(3-HYDROXYMETHYL-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl (3-hydroxymethyl-benzyl)-carboxylate from 3-(N-Boc-aminomethyl)benzoic acid: Boc-Mamb-OH (1.765 g, 7.02 mmol) was dissolved in 20 mL of anhydrous THF and cooled in an ice-water bath to 0°C. Subsequently, N-methylmorpholine (0.77 mL, 7.0 mmol) and isobutyl chloroformate (0.91 mL, 7.0 mmol). The reaction mixture was stirred in an ice bath for 10 min before being filtered through a medium porosity glass filter and the precipitate was washed with 2 × 10 mL of anhydrous THF. The filtrate was re-placed in an ice-water bath and cooled, and sodium borohydride (0.815 g, 21.5 mmol) was added, followed by the slow addition of 10 mL of methanol. The reaction was continued for 30 min and then the mixture was concentrated to dryness. The residue was resuspended in 80 mL of ethyl acetate and washed sequentially with 2 x 40 mL of aqueous 1 M sodium bisulfate, 2 x 40 mL of saturated aqueous sodium bicarbonate and 40 mL of brine. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to dryness to afford the target compound tert-butyl (3-hydroxymethyl-benzyl)-carboxylate (1.542 g, 6.51 mmol, 93% yield).ESI(+)MS m/z: 260 [M+Na]+.

References

[1] Patent: WO2008/5457, 2008, A2. Location in patent: Page/Page column 56
[2] Patent: WO2011/21209, 2011, A1. Location in patent: Page/Page column 69; 72
[3] Patent: US2012/101099, 2012, A1. Location in patent: Page/Page column 28; 30
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 946 - 979
[5] Patent: WO2004/89892, 2004, A2. Location in patent: Page 106

(3-HYDROXYMETHYL-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER(226070-69-5)Related Product Information

• (4-HYDROXYMETHYL-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER
• 3-(1-(TERT-BUTOXYCARBONYL)PIPERIDIN-2-YL)BENZOIC ACID
• Boc-3-Aminomethylbenzoic acid
• RARECHEM GT HW 0095
• 4-AMINO-3-(BOC-AMINOMETHYL)-BENZOIC ACID
• 2-(TERT-BUTOXYCARBONYL)-1,2,3,4-TETRAHYDROISOQUINOLINE-7-CARBOXYLIC ACID
• 2-(3-CARBOXY-PHENYL)-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 2-(TERT-BUTOXYCARBONYL)ISOINDOLINE-5-CARBOXYLIC ACID
• 3-(BOC-AMIDINO)-BENZOIC ACID
• (3-HYDROXYMETHYL-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER
• 3,4-DIHYDRO-1H-ISOQUINOLINE-2,5-DICARBOXYLIC ACID 2-TERT-BUTYL ESTER
• FMOC-4-AMINO-3-(BOC-AMINOMETHYL)-BENZOIC ACID
• 2-(3-METHOXYCARBONYL-2-METHYL-PHENYL)-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER