Tetrahydro-4H-pyran-4-one → HCID 67221139, compound

HRID 1798933Notes

Reaction equation

HRID 1798933 reaction equation
[ClH:1].[F:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:8](=[O:10])[O:9][C:5]=2[CH:4]=1.[O:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.C([BH3-])#N.[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].CO>[ClH:1].[F:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]([CH:11]3[CH2:12][CH2:13][N:14]([CH:22]4[CH2:23][CH2:24][O:19][CH2:20][CH2:21]4)[CH2:15][CH2:16]3)[C:8](=[O:10])[O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 86653876HCID 86653876, compound

Product 1

HCID 67221139HCID 67221139, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,3-benzoxazol-2(3H)-one hydrochloride D6 (270 mg), tetrahydropyran-4-one (200 mg), and titanium tetraisopropoxide (0.6 mL) was stirred at room temperature for 1 h and then methanol (4 mL) and sodium cyanoborohydride (120 mg) were added. After a further 2 h the product was isolated by SCX chromatography and further purified by chromatography on silica gel eluting with 0-10% 2M methanolic ammonia-dichloromethane. Conversion to the hydrochloride salt gave 6-fluoro-3-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,3-benzoxazol-2(3H)-one hydrochloride E2 (40 mg).

Workup

  1. customAfter a further 2 h the product was isolated by SCX chromatography
  2. customfurther purified by chromatography on silica gel eluting with 0-10% 2M methanolic ammonia-dichloromethane

Sources & evidence

ORD record
ord-10b6e587660744efa9f93dc6dcc36684
Source dataset
uspto-grants-2013_01
Patent number
US08344000B2

Reaction notes

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