Tetrahydrofuran → HCID 15454922, compound

HRID 2287531Notes

Reaction equation

HRID 2287531 reaction equation
C(OC([N:11]1[CH2:16][C@@H:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14][C@H:13]([NH:21][CH2:22][C:23]2[CH:28]=[C:27]([O:29][C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:25][C:24]=2[O:34][CH3:35])[C@@H:12]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=O)C1C=CC=CC=1.C1COCC1>[OH-].[OH-].[Pd+2].CO>[CH3:20][O:19][C:17]([C@@H:15]1[CH2:16][NH:11][C@@H:12]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C@@H:13]([NH:21][CH2:22][C:23]2[CH:28]=[C:27]([O:29][C:30]([F:33])([F:31])[F:32])[CH:26]=[CH:25][C:24]=2[O:34][CH3:35])[CH2:14]1)=[O:18]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 15454920HCID 15454920, compound

Product 1

HCID 15454922HCID 15454922, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S*,3S*,5S*)-1-benzyloxycarbonyl-5-methoxycarbonyl-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-2-phenylpiperidine (1.007 g, 1.758 mmol) and 20% Pd(OH)2 /C (0.258 g), THF (5.0 ml), and MeOH (30.0 ml) was stirred under an atmosphere of H2 (baloon) at room temperature for an hour. The catalyst was filtered off by the aid of Celite, and washed with THF. The combined filtrate and THF washings were concentrated in vacuo to give title compound (0.789 g, quantitatively) as a pale yellow oil. IRmax (film): 3340(s), 1735(s), 1718(s), 1608(m), 1250(br., s), 1150(br., s), 1033(s), 810(m), 750(m), 700(m) cm-1 ; 1H-NMR δ: 7.36-7.18(m, 5H), 7.00(dd, J=9.2, 2.2 Hz, 1H), 6.84(d, J=2.2 Hz, 1H), 6.62(d, J=9.2 Hz, 1H), 3.89(d, J=2.2 Hz, 1H), 3.71(s, 3H), 3.68(d, J=14.3 Hz, 1H), 3.51(ddd, J=11.9, 3.7, 1.8 Hz, 1H), 3.47(s, 3H), 3.40(d, J=14.3 Hz, 1H), 3.05(dddd, J=12.3, 11.9, 3.7, 3.7 Hz, 1H), 2.92-2.82(m, 1H), 2.88(dd, J=11.9, 11.9 Hz, 1H), 2.37(dm, J=13.6 Hz, 1H), 1.78(ddd, J=13.6, 12.3, 2.9 Hz, 1H), 1.68(br.s, 2H, NH×2) ppm.

Workup

  1. filtrationThe catalyst was filtered off by the aid of Celite
  2. washwashed with THF
  3. concentrationThe combined filtrate and THF washings were concentrated in vacuo

Sources & evidence

ORD record
ord-52040a0a9c9c44ed8bdc23a6fa991e1c
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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