Formaldehyde → HCID 66876833, compound

HRID 503947Notes

Reaction equation

HRID 503947 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15]1[CH2:19][CH2:18][C@@H:17]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])=[CH:31][CH:30]=3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH2:16]1)=O)(C)(C)C.C=O.C([BH3-])#N.[Na+]>C(Cl)Cl>[C:39]([Si:36]([CH3:38])([CH3:37])[O:35][C:32]1[CH:31]=[CH:30][C:29]([S:26]([C:23]2[CH:24]=[CH:25][C:20]([C@@H:17]3[CH2:18][CH2:19][N:15]([CH3:13])[CH2:16]3)=[CH:21][CH:22]=2)(=[O:27])=[O:28])=[CH:34][CH:33]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 66877225HCID 66877225, compound

Product 1

HCID 66876833HCID 66876833, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of (S)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-benzenesulfonyl]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (342 mg, 0.661 mmol) in DCM (5 mL) under argon atmosphere. The mixture was stirred at room temperature for 75 minutes, then solvent was evaporated under reduced pressure. The crude material (482.9 mg) was dissolved in acetonitrile (5 mL) and to the resulting solution, under argon atmosphere, was added formaldehyde (37% in water, 0.264 mL, 3.292 mmol) followed by sodium cyanoborohydride (82.4 mg, 1.316 mmol). The reaction mixture was stirred at room temperature for 1.5 hours, then buffered to pH 12. The resulting mixture was extracted with DCM, and the combined organic extracts were dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (DCM/MeOH/NH4OH) to give 248.2 mg (87% yield) of (S)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-benzenesulfonyl]-phenyl}-1-methyl-pyrrolidine as a colorless oil which solidified upon standing.

Workup

  1. customsolvent was evaporated under reduced pressure
  2. dissolutionThe crude material (482.9 mg) was dissolved in acetonitrile (5 mL) and to the resulting solution, under argon atmosphere
  3. stirringThe reaction mixture was stirred at room temperature for 1.5 hours
  4. extractionThe resulting mixture was extracted with DCM
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting crude material was purified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-247fd11aaff94bc8ae4d0d61bd00e16c
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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