Sodium Azide → HCID 86756518, compound

HRID 1531494Notes

Reaction equation

HRID 1531494 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]OS(C)(=O)=O)=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:54]=[N+:55]=[N-:56].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:15]=[CH:16][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:18][CH:19]=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][N:54]=[N+:55]=[N-:56])=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86756517HCID 86756517, compound

Product 1

HCID 86756518HCID 86756518, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 0.200 g (0.266 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 in 1.8 ml of absolute N,N-dimethylformamide was treated with 0.025 g (0.398 mmol, 1.5 equiv.) of anhydrous sodium azide, and stirred for 45 min. at 50° C. The reaction mixture was then 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 3:1 mixture of hexane and ethyl acetate as the eluent and yielded 0.162 g (0.231 mmol, 86.8% of theory) of (3R,4R)-3-[1-(3-azido-propyl)-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: 700 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-5441ab2db7c14fc58f8301936ce9761b
Source dataset
uspto-grants-2001_03
Patent number
US06197959B1

Reaction notes

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