Water → HCID 86697532, compound

HRID 626840Notes

Reaction equation

HRID 626840 reaction equation
[Cl:1][C:2]1[C:12]([C:13]#[N:14])=[C:6]2[CH:7]=[N:8][CH2:9][CH2:10][O:11][C:5]2=[C:4]([CH:15]([OH:17])[CH3:16])[CH:3]=1.[BH4-].[Na+].O>C(O)C>[Cl:1][C:2]1[C:12]([C:13]#[N:14])=[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][O:11][C:5]2=[C:4]([CH:15]([OH:17])[CH3:16])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86697531HCID 86697531, compound

Product 1

HCID 86697532HCID 86697532, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 7-chloro-9-(1-hydroxyethyl)-2,3-dihydro-1,4-benzoxazepine-6-carbonitrile was taken up in ethanol (30 mL) cooled in an ice bath and the sodium tetrahydroborate (0.16 g, 4.4 mmol) was added. The reaction was allowed to stir for 1 h, and water was added to quench the remaining hydride and the reaction was concentrated to remove most of the ethanol. The residue was dissolved with ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated to give 7-chloro-9-(1-hydroxyethyl)-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile as an oil (0.45 g, 41%). LCMS calculated for C12H14ClN2O2(M+H)+: m/z=253.1; found: 253.0.

Workup

  1. temperaturecooled in an ice bath
  2. customto quench the remaining hydride
  3. concentrationthe reaction was concentrated
  4. customto remove most of the ethanol
  5. dissolutionThe residue was dissolved with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-010c3c52b38f4f43ad0b8c3c21f15b09
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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