HCID 69489276, compound → HCID 69489222, compound

HRID 1531499Notes

Reaction equation

HRID 1531499 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][C:49]#[N:50])=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[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][CH2:49][NH2:50])=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 69489276HCID 69489276, compound

Product 1

HCID 69489222HCID 69489222, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a well stirred solution of 0.130 g (0.190 mmol) of (3R,4R)-3-[1-(3-cyano-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester in 0.5 ml of absolute THF was added dropwise 1 ml of a 1M solution of borane-THF complex in THF. After stirring for 3 h at 70° C., the reaction was allowed to warm 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 140:10:1 v/v/v mixture of dichloromethane/methanol/28% ammonium hydroxide solution as the eluent to yield 0.090 g (0.131 mmol, 68.9% of theory) of (3R,4R)-3-[1-(4-amino-butyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester as a light yellow oil; MS: 688 (M+H)+.

Workup

  1. temperatureto warm 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 140:10:1 v/v/v mixture of dichloromethane/methanol/28% ammonium hydroxide solution as the eluent

Sources & evidence

ORD record
ord-270d43a1861048219c4317e4319132d0
Source dataset
uspto-grants-2001_03
Patent number
US06197959B1

Reaction notes

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