Sodium borohydride → (1'-Benzylspiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1-yl)methanol

HRID 2204069Notes

Reaction equation

HRID 2204069 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]3[C:23]([CH:26]=[O:27])=[CH:24][CH:25]=[C:14]23)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]3[C:23]([CH2:26][OH:27])=[CH:24][CH:25]=[C:14]23)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 585509691'-Benzylspiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1-carbaldehyde

Product 1

HCID 58550905(1'-Benzylspiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1-yl)methanolYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1′-benzylspiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbaldehyde (1.94 g, 5.40 mmol) in methanol (40 mL) was cooled to 0° C. Sodium borohydride (409 mg, 10.8 mmol) was added in one portion and the cooling bath was removed. After stirring for 1 h at room temperature, the reaction was diluted with saturated aqueous NaHCO3 (50 mL) and DCM (150 mL). The organic layer was separated and the aqueous layer was extracted twice more with DCM (150 mL). The organic layers were combined, dried, filtered and concentrated to give (1′-benzylspiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-yl)methanol (1.66 g) as a white solid. The crude material was used in the next step without purification.

Workup

  1. customthe cooling bath was removed
  2. additionthe reaction was diluted with saturated aqueous NaHCO3 (50 mL) and DCM (150 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice more with DCM (150 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3179ba7ec8104b19b45ea28bfefcbb36
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

Loading…