Ethanol → tert-Butyl 2-hydroxy-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate

HRID 23714Notes

Reaction equation

HRID 23714 reaction equation
[O:1]=[C:2]([C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1)[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(O)C.[BH4-].[Na+]>C1COCC1>[OH:1][CH:2]([C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[CH:17][CH:18]=1)[CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 22574343tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate

Product 1

HCID 22574361tert-Butyl 2-hydroxy-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate (1.41 g, 4.22 mmol) was stirred under N2 in dry THF (25 ml) and absolute ethanol (2 ml). Sodium borohydride (0.16 g, 4.23 mmol) was added and the reaction stirred for 18 hr then the solvents evaporated. The residue was chromatographed over silica gel (90 g) eluting with 50% ethyl acetate-hexane. The product was obtained (1.0 g, 71%) as a clear gum which slowly crystallized to give a white solid.

Workup

  1. customthe solvents evaporated
  2. customThe residue was chromatographed over silica gel (90 g)
  3. washeluting with 50% ethyl acetate-hexane
  4. customThe product was obtained (1.0 g, 71%) as a clear gum which
  5. customslowly crystallized
  6. customto give a white solid

Sources & evidence

ORD record
ord-d6286e356ac648b9923041f6c7752b4b
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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