Sodium borohydride → HCID 57855474, compound

HRID 1360649Notes

Reaction equation

HRID 1360649 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH2:15][C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])(=[O:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([S:12]([CH2:15][CH:16]([OH:17])[CH2:18][O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:14])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57855498HCID 57855498, compound

Product 1

HCID 57855474HCID 57855474, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1-[(7-chloro-3,4-dihydroisoquinolin-2(1H)-yl)sulfonyl]-3-phenoxyacetone (468 mg, 1.23 mmol) was prepared in MeOH (15 ml), then NaBH4 (77 mg, 1.85 mmol) was added portionwise. The resulting mixture was stirred at RT for 1 h00. The reaction mixture was concentrated under reduced pressure, then diluted with EtOAc (30 ml) and washed with a 1N aqueous solution of HCl (15 ml) and a saturated aqueous solution of NaHCO3 (15 ml). The aqueous layers were extracted with EtOAc (30 ml). The organic layers were combined, dried (MgSO4) and the solvent was removed under reduced pressure. After purification by crystallization in EtOAc/pentane, the title compound was obtained as a white powder (415 mg, 88%). HPLC, Rt: 4.5 min (purity: 99.2%). LC/MS, M+(ESI): 382.2.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with EtOAc (30 ml)
  3. washwashed with a 1N aqueous solution of HCl (15 ml)
  4. extractionThe aqueous layers were extracted with EtOAc (30 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customAfter purification
  8. customby crystallization in EtOAc/pentane

Sources & evidence

ORD record
ord-41afe13165e6413a8548fedd3b16d51c
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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