Trifluoroacetic acid → HCID 66865000, compound

HRID 222578Notes

Reaction equation

HRID 222578 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH2:24][CH2:25][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:27][CH:28]=3)=[CH:19][CH:18]=2)[CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:32][S:29]([N:26]1[CH2:25][CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH3:15])=[CH:18][CH:19]=2)[CH2:28][CH2:27]1)(=[O:30])=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66864788HCID 66864788, compound

Product 1

HCID 66865000HCID 66865000, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{1-[4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (1.16 g, 2.50 mmol) in dichloromethane (25 mL) is added trifluoroacetic acid (1.32 mL, 17.48 mmol). The reaction is stirred at room temperature for 18 h. The mixture is concentrated in vacuo and diluted with 3 mL of ethyl acetate. 2 M aqueous sodium hydroxide is added to produce a white solid. The solid is filtered and dried to afford 0.86 g of the title compound. MS (m/z) 365 (M+1). The title compound (0.320 g, 0.88 mmol) is separated into its enantiomers using an eluent of 0.2% dimethylethylamine in 2:3 acetonitrile:methanol on a 4.6×150 mm Chiralcel AD-H column at 1 mL/min to afford 0.115 g of isomer 1 (100% ee, RT=5.27 min) MS (m/z) 365 (M+1) and 0.112 g of isomer 2 (100% ee, RT=8.59 min). MS (m/z) 365 (M+1).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additiondiluted with 3 mL of ethyl acetate
  3. addition2 M aqueous sodium hydroxide is added
  4. customto produce a white solid
  5. filtrationThe solid is filtered
  6. customdried

Sources & evidence

ORD record
ord-ab2b62802c974fdd8b790aa6330f406c
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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