Dichloromethane → HCID 69332896, compound

HRID 354417Notes

Reaction equation

HRID 354417 reaction equation
C(C[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C@@H:13]2[CH2:17][C@H:16]([O:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)[CH2:15][N:14]2C(OC(C)(C)C)=O)=[N:9][CH:10]=1)(O)=O.[C:36]([OH:42])(C(F)(F)F)=[O:37].[CH2:43](Cl)Cl>>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[O:18][C@@H:16]1[CH2:15][NH:14][C@H:13]([CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:36]([O:42][CH3:43])=[O:37])=[CH:10][N:9]=2)[CH2:17]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69333141HCID 69333141, compound

Product 1

HCID 69332896HCID 69332896, compoundYield 80%

Procedure

To a stirred solution of 5-carboxymethyl-2-[(2S,4S)-1-tert-butoxycarbonyl-4-(2-napthyloxy)-2-pyrrolidinyl]methoxypyridine (170 mg, 0.36 mmol) in CH2Cl2 (5 ml) was added TFA (2 ml) at room temperature. After 2 h stirring, the mixture was concentrated in vacuo, which was diluted with CH2Cl2 and basified by the addition of 1 N NaOH. The combined reaction mixture was extracted with CH2Cl2. The organic layer was washed with brine, which were dried over NaSO4 and concentrated. The residue was purified on TLC [CHCl3/MeOH (10/1)], to give methyl 2-[(2S,4S)-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxypyridine-5-carboxylate (107 mg, 80%) as a colorless oil 1H-NMR (CDCl3) δ1.95 (m, 1H), 2.27 (br, 1H), 2.46 (m, 1H), 3.19 (dd, J=12.2, 4.9 Hz, 1H), 3.41 (d, J=12.2 Hz, 1H), 3.65 (m, 1H), 3.89 (s, 3H), 4.58 (m, 2H), 5.00 (br, 1H), 6.77 (d, J=8.8 Hz, 1H), 7.06 (br, 1H), 7.11 (dd, J=8.8, 2.7 Hz, 1H), 7.31-7.45 (m, 2H), 7.69-7.76 (m, 3H), 8.13 (dd, J=8.8, 2.4 Hz, 1H), 8.78 (d, J=2.2 Hz, 1H).

Workup

  1. concentrationthe mixture was concentrated in vacuo, which
  2. additionwas diluted with CH2Cl2
  3. additionbasified by the addition of 1 N NaOH
  4. customThe combined reaction mixture
  5. extractionwas extracted with CH2Cl2
  6. washThe organic layer was washed with brine, which
  7. dry with materialwere dried over NaSO4
  8. concentrationconcentrated
  9. customThe residue was purified on TLC [CHCl3/MeOH (10/1)]

Sources & evidence

ORD record
ord-85177be5db7d4b599d030e60bd106ee4
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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