Sodium Carbonate → benzyl N-((2S)-1-hydroxybutan-2-yl)carbamate

HRID 722798Notes

Reaction equation

HRID 722798 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].C([O-])([O-])=O.[Na+].[Na+].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(C)=O.O>[CH2:13]([O:20][C:21]([NH:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 1200842-Amino-1-butanol, (+)-

Product 1

HCID 10263004benzyl N-((2S)-1-hydroxybutan-2-yl)carbamateYield 43%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of (S)-2-amino-1-butanol (2.0 g, 22.5 mmol) in acetone/H2O 1:1 (50 mL), Na2CO3 (8.7 g, 81.9 mmol) and BnOCOCl (5.8 g, 33.8 mmol) were added. After stirring at 0° C. for 1 h, the solid was filtered off and washed with acetone (2×30 mL). The filtrates were concentrated in vacuo and the residue was purified by column chromatography on silica (100% CH2Cl2 to CH2Cl2/MeOH 20:1) to obtain alcohol 7 as a white solid (2.14 g, 43% yield).

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with acetone (2×30 mL)
  3. concentrationThe filtrates were concentrated in vacuo
  4. customthe residue was purified by column chromatography on silica (100% CH2Cl2 to CH2Cl2/MeOH 20:1)

Sources & evidence

ORD record
ord-1b49667fa4ad4a41b9df00f4f7dea862
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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