Aluminium lithium hydride → tert-butyl N-[1-oxo-3-(4-phenylmethoxyphenyl)propan-2-yl]carbamate

HRID 852877Notes

Reaction equation

HRID 852877 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:36])[NH:13][CH:14]([C:30](=[O:35])N(OC)C)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12](=[O:36])[NH:13][CH:14]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:21]=1)[CH:30]=[O:35])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23001393(RS)-[2-(4-Benzyloxy-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 10904373tert-butyl N-[1-oxo-3-(4-phenylmethoxyphenyl)propan-2-yl]carbamateYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (916 mg, 24.1 mmol) was added cautiously and portionwise during 15 min to a stirred solution of (RS)-[2-(4-Benzyloxy-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (10.00 g, 24.1 mmol) in THF (150 mL) at 0° C. under an atmosphere of argon. The ice-bath was removed and the mixture was stirred for 1 hr, then poured onto a mixture of ice and KHSO4 (1 M aq.). When the ice had melted the product was extracted into EtOAc. The combined extracts were washed with brine then dried (Na2SO4) and evaporated to give (RS)-[1-(4-Benzyloxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (8.51 g, 99%), mp 100.3-101.7° C. 1H NMR (CDCl3) δ 1.44 (s, 9H), 3.07 (d, J=6.7 Hz, 2H), 4.40 (br s, 1H), 5.05 (s, 2H), 6.92 (d, J=8.6 Hz, 2H), 7.09 (d, J=8.7 Hz, 2H), 7.33-7.45 (m, 5H), 9.63 (s, 1H). 13C NMR (CDCl3) δ 199.6, 156.4, 144.4, 136.8, 130.4, 128.6, 128.5, 128.0, 127.9, 127.5, 115.1, 80.9, 70.0, 46.0, 34.6, 28.3.

Workup

  1. customThe ice-bath was removed
  2. additionpoured onto a mixture of ice and KHSO4 (1 M aq.)
  3. extractionwas extracted into EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialthen dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0d9db2659f68431e9e2dcbb7d5a7e000
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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