Triethylamine → 4-Piperidinemethanol, 1-benzoyl-

HRID 1068238Notes

Reaction equation

[C:1]([N:9]1[CH2:17][CH2:16][CH:12]([C:13](O)=[O:14])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.CN(C=O)C.O>[OH:14][CH2:13][CH:12]1[CH2:11][CH2:10][N:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2 g of 1-benzoyl-isonipecotic acid (step A) in 50 mL THF at 0° C. were added 1.47 g of triethylamine and 1.99 g of isobutyl chloroformate. The reaction was stirred for 1 hr at 0° C. To a solution of 1.10 g of sodium borohydride in 30 ml DMF at 0° C. was slowly added the above THF mixture. The reaction was again stirred for 1 hr at 0° C. Water (80 mL) was slowly added to the reaction and the mixture was extracted with 5×80 mL of EtOAc and the combined organic layers were dried over MgSO4. The solvent was then evaporated under reduced pressure. The residue was purified by flash chromatography with 1:1 hexane EtOAc followed by hexane:EtOAc:MeOH, 50:50:5 to give 1.865 g of the title compound. ESI-MS 219.9 (M+H); HPLC A: 2.34 min.

Workup

stirringThe reaction was again stirred for 1 hr at 0° C
extractionthe mixture was extracted with 5×80 mL of EtOAc
dry with materialthe combined organic layers were dried over MgSO4
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by flash chromatography with 1:1 hexane EtOAc

Sources & evidence

ORD record: ord-ae1e2022d81641bca5f5ad97ae64b0af
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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