Di-tert-butyl dicarbonate → HCID 22288417, compound

HRID 968243Notes

Reaction equation

HRID 968243 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O>C(Cl)Cl>[OH:10][CH2:9][C:4]1[CH:3]=[C:2]([NH:1][C:12](=[O:11])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 15680639(3-Amino-5-methylphenyl)methanol

Product 1

HCID 22288417HCID 22288417, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-5-methylphenyl)methanol (1.0 g, 7.29 mmol) in CH2Cl2 (30 mL) was added BOC2O (1.75 g, 8.02 mmol) at room temperature. After 24 hours the mixture was concentrated. Flash column chromatography (30% EtOAc/hexanes) gave tert-butyl 3-(hydroxymethyl)-5-methylphenylcarbamate as a white solid. 1H-NMR (300 MHz, CDCl3) δ 7.20 (s, 1H), 7.18 (s, 1H), 6.85 (s, 1H), 6.45 (bs, 1H), 4.60 (s, 2H), 3.60 (bs, 2H), 2.32 (s, 3H), 1.50 (s, 9H).

Workup

  1. concentrationAfter 24 hours the mixture was concentrated

Sources & evidence

ORD record
ord-5f1ba161f00d4675b95c778570c57176
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

Loading…