Formaldehyde → 4-{[(2S)-2-Hydroxypropyl](methyl)amino}butyric acid tert.-butyl ester

HRID 1926911Notes

Reaction equation

HRID 1926911 reaction equation
C=O.[C:3]([BH3-])#N.[Na+].[C:7]([O:11][C:12](=[O:21])[CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C@@H:18]([OH:20])[CH3:19])([CH3:10])([CH3:9])[CH3:8].O>CO.ClCCl>[C:7]([O:11][C:12](=[O:21])[CH2:13][CH2:14][CH2:15][N:16]([CH2:17][C@@H:18]([OH:20])[CH3:19])[CH3:3])([CH3:8])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 580168024-{[(2S)-2-Hydroxypropyl]amino}butyric acid tert.-butyl ester

Product 1

HCID 580169214-{[(2S)-2-Hydroxypropyl](methyl)amino}butyric acid tert.-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Add 0.62 ml (670 mg, 7.81 mmol) of 35% aqueous formaldehyde solution and 101 mg (1.61 mmol) sodium cyanoborohydride to a solution of 350 mg (1.61 mmol) 4-{[(2S)-2-hydroxypropyl]amino}butyric acid tert.-butyl ester in 10 ml methanol. Stir the reaction mixture for 16 h at room temperature. After adding 30 ml water and 40 ml dichloromethane, dry the organic phase over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation, and dry. 323 mg (81% of theor.) of the desired product is obtained.

Workup

  1. dry with materialdry the organic phase over sodium sulphate
  2. filtrationfilter
  3. concentrationConcentrate the filtrate
  4. customby vacuum evaporation
  5. customdry

Sources & evidence

ORD record
ord-d962a9c819d245a9b33ffe1953557186
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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