Sodium borohydride → HCID 71128815, compound

HRID 1468861Notes

Reaction equation

HRID 1468861 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[CH:24][C:3]=1[CH2:4][O:5][CH2:6][C@@H:7]1[CH2:9][C@@H:8]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][N:17]=2)[CH2:12][CH2:11]1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[CH:24][C:3]=1[CH2:4][O:5][CH2:6][C@@H:7]1[CH2:9][C@@H:8]1[CH:10]1[CH2:11][CH2:12][N:13]([C:16]2[N:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][N:17]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71473972HCID 71473972, compound

Product 1

HCID 71128815HCID 71128815, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4-((1R,2R)-2-(((2-fluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl) piperidin-1-yl)pyrimidine-5-carbaldehyde (Step E product, 200 mg, 0.447 mmol) was dissolved in MeOH (20 ml) at RT and NaBH4 (66.2 mg, 0.670 mmol) was added. The mixture was stirred at RT for 30 min and TLC showed the SM was completely consumed. The mixture was diluted with EtOAc, washed with water, dried over MgSO4, evaporated to afford 198 mg of the product (99%) which was used for the next step. LC/MS (m/z): 450 (M+H)+.

Workup

  1. customwas completely consumed
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-329190b9c0e645978b9a8fea9b5e0f41
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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