Sodium cyanoborohydride → (R)-tert-butyl 1-(4-methyloxazol-2-yl)ethylcarbamate

HRID 2070998Notes

Reaction equation

HRID 2070998 reaction equation
I[CH2:2][C:3]1[N:4]=[C:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[O:6][CH:7]=1.[BH3-]C#N.[Na+]>CN(P(N(C)C)(N(C)C)=O)C>[CH3:2][C:3]1[N:4]=[C:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[O:6][CH:7]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 68670282tert-butyl N-[(1R)-1-[4-(iodomethyl)-1,3-oxazol-2-yl]ethyl]carbamate

Product 1

HCID 68670958(R)-tert-butyl 1-(4-methyloxazol-2-yl)ethylcarbamateYield 38%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of (R)-tert-butyl 1-(4-(iodomethyl)oxazol-2-yl)ethylcarbamate (660 mg, 1.87 mmol) in HMPA (10 mL), was added NaCNBH3 (470 mg, 7.5 mmol). The reaction was stirred for 4 h. and poured into ice-cold water and extracted with hexanes. The organic layer was dried on Na2SO4, concentrated, and chromatographed on silica gel (10% ethyl acetate/90% hexanes) to yield 38% of (R)-tert-butyl 1-(4-methyloxazol-2-yl)ethylcarbamate.

Workup

  1. additionpoured into ice-cold water
  2. extractionextracted with hexanes
  3. customThe organic layer was dried on Na2SO4
  4. concentrationconcentrated
  5. customchromatographed on silica gel (10% ethyl acetate/90% hexanes)

Sources & evidence

ORD record
ord-399964b100064ec5a091e520cb796062
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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