Sodium borohydride → 1-(7-Chloro-6-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepin-9-yl)ethanol

HRID 626817Notes

Reaction equation

HRID 626817 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])[CH3:15])[C:5]2[O:11][CH2:10][CH2:9][N:8]=[CH:7][C:6]=2[C:12]=1[CH3:13].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([OH:16])[CH3:15])[C:5]2[O:11][CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866975131-(7-Chloro-6-methyl-2,3-dihydro-1,4-benzoxazepin-9-yl)ethanone

Product 1

HCID 866975141-(7-Chloro-6-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepin-9-yl)ethanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(7-Chloro-6-methyl-2,3-dihydro-1,4-benzoxazepin-9-yl)ethanone (630 mg, 2.6 mmol) was stirred in methanol (20 mL) and cooled to 0° C. Sodium tetrahydroborate (150 mg, 4.0 mmol) was added. The mixture was stirred for 1 hour at room temperature and evaporated. The mixture was extracted with ethyl acetate, washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated gave the desired compound (580 mg, 90%). LCMS calculated for C12H17ClNO2 (M+H)+: m/z=242.1; found: 242.0.

Workup

  1. customevaporated
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c576c389c45d4d34924bfe5aec4b848e
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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