Methanol → HCID 69488943, compound

HRID 1531503Notes

Reaction equation

HRID 1531503 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][CH2:48][O:49]S(C)(=O)=O)=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:56]O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][CH2:48][O:49][CH3:56])=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 86756517HCID 86756517, compound

Product 1

HCID 69488943HCID 69488943, compoundYield 65.2%

Conditions

Temperature
50 °C

Procedure

To an ice cooled solution of 0.240 g (0.319 mmol) of crude (3R,4R)-3-[1-(3-methanesulfonyloxy-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester [example 10(a)] in 3 ml of absolute methanol was added 0.0 17 g (0.383, 1.2 equiv.) of sodium hydride (55% suspension in mineral oil). The reaction was then stirred for 6 h at 50° C., allowed to cool to room temperature, poured into 50 ml of an ice/water mixture and extracted three times with 50 ml of ethyl acetate. The combined organic phases were washed twice with 20 ml of water, evaporated under reduced pressure and dried in a high vacuum. The thus obtained crude product was purified by chromatography on silica gel using a 2:1 v/v mixture of hexane and ethyl acetate as eluent to yield 0.143 g (0.208 mmol, 65.2% of theory) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[1-(3-methoxy-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil; MS: 689 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted three times with 50 ml of ethyl acetate
  3. washThe combined organic phases were washed twice with 20 ml of water
  4. customevaporated under reduced pressure
  5. customdried in a high vacuum
  6. customThe thus obtained crude product
  7. customwas purified by chromatography on silica gel using
  8. additiona 2:1 v/v mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-b95bcf49d06b46d8b9320a1f92352457
Source dataset
uspto-grants-2001_03
Patent number
US06197959B1

Reaction notes

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