Trifluoroacetic acid → HCID 21839784, compound

HRID 2256028Notes

Reaction equation

HRID 2256028 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 21839966HCID 21839966, compound

Product 1

HCID 21839784HCID 21839784, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-hydroxy-4-(2-methoxyphenyl)piperidine (2.59 g) in dichloromethane (45 mL) was treated with trifluoroacetic acid (8.6 g) followed by triethylsilane (17.5 g). The resulting brown reaction mixture was stirred for 5 minutes and then poured into a saturated solution of sodium bicarbonate. The bicarbonate solution was extracted with dichloromethane. The dichloromethane solution was dried and evaporated to give the des-hydroxy compound (2.1 g); NMR (CDCl3): 1.55-1.66 (m, 2), 1.78-1.82 (br, 2), 2.91, (m, 2), 3.11 (m, 1), 3.8 and 3.82 (s, 3), 4.32 (br, 2), 5.12-5.28 (m, 2), 6.84 (d, 4, J=9), 6.87-6.95 (m, 1), 7.11-7.25 (m, 2), 7.29-7.38 (m, 5); MS: m/z=326(M+1). This material was used in the next step without further purification.

Workup

  1. extractionThe bicarbonate solution was extracted with dichloromethane
  2. dry with materialThe dichloromethane solution was dried
  3. customevaporated
  4. customto give the des-hydroxy compound (2.1 g)
  5. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-151ec80613f54a9bbd470574fd6a555f
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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