Tetrahydrofuran → tert-Butyl (S)-(4-hydroxy-1-methoxybutan-2-yl)carbamate

HRID 1182120Notes

Reaction equation

HRID 1182120 reaction equation
C([O:8][C:9](=O)[CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][O:13][CH3:14])C1C=CC=CC=1.[Li+].[BH4-].C1COCC1>C(OCC)C>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:11]([CH2:12][O:13][CH3:14])[CH2:10][CH2:9][OH:8])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 57976545(S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester

Product 1

HCID 53259998tert-Butyl (S)-(4-hydroxy-1-methoxybutan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester (10.4 g, 32.3 mmol) in dry diethylether (70 ml) cooled to 0° C. is treated slowly with a 2.0 M solution of LiBH4 in THF (32.2 ml, 64.4 mmol). The reaction mixture is allowed to warm to ambient temperature and then left to stir. After 6 hours the reaction mixture is quenched slowly with 0.5 M aqueous solution of citric acid and extracted with ether. The ether phase is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (elution with a gradient 3:7 to 6:4 ethylacetate/hexane) to afford ((S)-3-Hydroxy-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester as a clear oil. [M-BOC] 120.13

Workup

  1. waitleft
  2. customAfter 6 hours the reaction mixture is quenched slowly with 0.5 M aqueous solution of citric acid
  3. extractionextracted with ether
  4. dry with materialThe ether phase is dried over magnesium sulphate
  5. customevaporated
  6. customThe crude product is purified by flash silica chromatography (
  7. washelution with a gradient 3:7 to 6:4 ethylacetate/hexane)

Sources & evidence

ORD record
ord-21cdab5396d74da699493784cc7af339
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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