Sodium borohydride → HCID 58295720, compound

HRID 390153Notes

Reaction equation

HRID 390153 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:29]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15](=[O:28])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:11][CH2:10]1)[CH2:8][C:7]2=[O:30].[BH4-].[Na+]>CO.C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:29]=1[C:9]1([CH2:10][CH2:11][N:12]([C:15](=[O:28])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:14]1)[CH2:8][CH:7]2[OH:30]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 44226677HCID 44226677, compound

Product 1

HCID 58295720HCID 58295720, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (E)-7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indene-1,4′-piperidin]-3(2H)-one (20 mg, 0.042 mmol) in MeOH (2 mL) and THF (2 mL) was added solid NaBH4 (12 mg). The mixture was stirred at rt for 3 h. The mixture was diluted with 10% aq citric acid and extracted with ether (2×30 mL). The combined ether extracts were dried over MgSO4 and concentrated. The residue was purified by prep HPLC to afford (±)-(E)-1-(7-bromo-3-hydroxy-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-yl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one (1.8 mg, 9%) as a solid. LC-MS Method 1 tR=1.83, min, m/z=480, 482; 1H NMR (CDCl3) 1.39 (m, 2H), 1.63 (m, 1H), 2.12 (m, 1H), 2.5-3.0 (4H), 3.36 (m, 1H), 4.16 (m, 1H), 4.82 (m, 1H), 5.23 (br s, 1H), 6.86 (d, 1H), 7.18 (m, 1H), 7.3-7.8 (6H), 7.95 (d, 1H).

Workup

  1. extractionextracted with ether (2×30 mL)
  2. dry with materialThe combined ether extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-40ab7365ceb14ff9b6a5888b4e02ecbd
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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