Methanol → HCID 86676361, compound

HRID 1409674Notes

Reaction equation

HRID 1409674 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]([OH:16])=[O:15])[C@H:10]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:9]1)=O)(C)(C)C.S(Cl)([Cl:26])=O.[CH3:28]O>>[ClH:26].[F:23][C:20]1[CH:21]=[CH:22][C:17]([C@H:10]2[C@H:11]([C:14]([O:16][CH3:28])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67232495HCID 67232495, compound

Product 1

HCID 86676361HCID 86676361, compound

Procedure

(3R*,4R*)-1-tert-butoxycarbonyl-3-(4-fluorophenyl)piperidine-4-carboxylic acid (2.00 g, 6.19 mmol, prepared according to the procedure disclosed in WO 02/068387) in MeOH (20 ml) was treated dropwise with thionyl chloride (0.497 ml, 6.80 mmol) at rt. The mixture was stirred at rt for 12 h and then concentrated to afford the title compound. HPLC/MS: 238.0 (M+1); Rt=0.29 min.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-31a5f6afc53c460ea047b411e359ccdf
Source dataset
uspto-grants-2014_12
Patent number
US08921394B2

Reaction notes

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