Sodium cyanoborohydride → (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-{3-[N-5-(4,4,5,5,5-pentafluoropentylsulfinyl)pe ntylamino]propyl}chroman

HRID 1792336Notes

Reaction equation

HRID 1792336 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][O:17][CH3:18])=[CH:12][CH:13]=2)[O:8][CH2:7][C:6]1([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][O:28][CH3:29])=[CH:22][CH:21]=1)[CH3:19].[F:30][C:31]([F:47])([C:43]([F:46])([F:45])[F:44])[CH2:32][CH2:33][CH2:34][S:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=O)=[O:36].C([BH3-])#N.[Na+].C(Cl)(Cl)Cl.CO.O.N>CO.O>[CH3:18][O:17][CH2:16][O:15][C:11]1[CH:10]=[C:9]2[C:14]([CH:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][S:35]([CH2:34][CH2:33][CH2:32][C:31]([F:47])([F:30])[C:43]([F:44])([F:45])[F:46])=[O:36])[C:6]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][O:28][CH3:29])=[CH:24][CH:25]=3)([CH3:19])[CH2:7][O:8]2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 220333425-(4,4,5,5,5-Pentafluoropentylsulfinyl)pentanalHCID 22033411(3RS,4RS)-4-(3-aminopropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanHCID 160233799HCID 160233799, compound

Product 1

HCID 22033209(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-{3-[N-5-(4,4,5,5,5-pentafluoropentylsulfinyl)pe ntylamino]propyl}chromanYield 29.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of (3RS,4RS)-4-(3-aminopropyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (80 mg, 0.20 mmol) and 5-(4,4,5,5,5-pentafluoropentylsulfinyl)pentanal (80 mg, 0.19 mmol) in methanol (5 ml) was added a solution of sodium cyanoborohydride (12 mg, 0.19 mmol) in methanol (5 ml), which was then stirred at 0 for 2 hours. The reaction solution was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to preparative TLC on silica gel using chloroform/methanol/ammonia water (7/1/0.1) as a mobile phase to give (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-{3-[N-5-(4,4,5,5,5-pentafluoropentylsulfinyl)pe ntylamino]propyl}chroman (38 mg, yield 28%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThis crude product thus obtained

Sources & evidence

ORD record
ord-6920b1e3a81b432baa70093baeedbeea
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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