Sodium borohydride → HCID 57512075, compound

HRID 348924Notes

Reaction equation

HRID 348924 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:5][C@H:6]([NH:20][C:21]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][C:26]2=[O:32])=[O:22])[C@H:7]([OH:19])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH3:18])[CH:12]=1.CCCCCC(COC(C1C=CN=CC=1)=O)C.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:5][C@H:6]([NH:20][C:21]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH:26]2[OH:32])=[O:22])[C@H:7]([OH:19])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH3:18])[CH:12]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 9856112HCID 9856112, compoundHCID 57512074N-{(1S,2R)-1-(3,5-Difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-3-oxoindane-5-carboxamide

Product 1

HCID 57512075HCID 57512075, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-3-oxoindane-5-carboxamide prepared by the method in EXAMPLE SP-201 (66 mg, 0.13 mmol) in methanol (3 mL) is added sodium borohydride (20 mg, 0.52 mmol). The reaction stirred at room temperature 3 h. The reaction is concentrated under reduced pressure, redissolved in water (3 mL) and partitioned into ethyl acetate. The organic layer is washed with water, saturated sodium bicarbonate, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 495.2 [M+H]+.

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. dissolutionredissolved in water (3 mL)
  3. custompartitioned into ethyl acetate
  4. washThe organic layer is washed with water, saturated sodium bicarbonate, and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e39734e180bc4a98891537c8502de5b1
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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