Tetrahydrofuran → (R)-tert-Butyl (4-hydroxybutan-2-yl)carbamate

HRID 1182121Notes

Reaction equation

HRID 1182121 reaction equation
C([O:8][C:9](=O)[CH2:10][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]I)C1C=CC=CC=1.[BH4-].[Li+].C1COCC1>C(OCC)C>[C:18]([O:17][C:15](=[O:16])[NH:14][C@H:11]([CH3:12])[CH2:10][CH2:9][OH:8])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 11258642Benzyl (S)-3-(Boc-amino)-4-iodobutanoate

Product 1

HCID 29928104(R)-tert-Butyl (4-hydroxybutan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (S)-3-tert-butoxycarbonylamino-4-iodo-butyric acid benzyl ester (0.2 g, 0.477 mmol) in dry diethylether (3 ml) cooled to 0° C. under argon, is treated with a 2.0 M solution of lithium borohydride in THF (0.95 ml, 1.9 mmol). The reaction mixture is allowed to warm to ambient temperature with stirring for 18 hours. The reaction is quenched by addition of water and partitioned between ethylacetate and 10% citric acid solution. The organic phase is washed with brine, dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 1% methanol in DCM as eluent to afford ((R)-3-hydroxy-1-methyl-propyl)-carbamic acid tert-butyl ester.

Workup

  1. customThe reaction is quenched by addition of water
  2. custompartitioned between ethylacetate and 10% citric acid solution
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe crude product is purified by flash silica chromatography

Sources & evidence

ORD record
ord-7e43bb4863ff4738ba3c86a72300c571
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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