Acetic Acid → HCID 86629213, compound

HRID 2384936Notes

Reaction equation

HRID 2384936 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[OH:12])=[C:4]([O:15][CH3:16])[CH:3]=1.C=O.[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@@H:7]2[CH2:11][N:10]([CH3:19])[CH2:9][C@H:8]2[OH:12])=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68950223HCID 68950223, compound

Product 1

HCID 86629213HCID 86629213, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dissolve 4-(4-bromo-2-methoxy-phenoxy)-pyrrolidin-3-ol (409 mg, 1.42 mmol) in dichloroethane (15 mL) and add formaldehyde (0.117 mL, 1.56 mmol, 37% aqueous solution), sodium triacetoxyborohydride (451 mg, 2.13 mmol), and acetic acid (0.325 mL, 5.68 mmol). Stir the mixture overnight. Dilute with saturated sodium bicarbonate and extract three times with dichloromethane. Combine all the organics and dry over sodium sulfate, filter, and evaporate the filtrate. Purify by silica gel chromatography, eluting with 0-6% MeOH in dichloromethane with 2 N ammonia to give 410 mg (95%) of the title compound as a clear oil. LC-MS/ES m/z (81Br) 304.0 [M+H]−.

Workup

  1. extractionextract three times with dichloromethane
  2. dry with materialdry over sodium sulfate
  3. filtrationfilter
  4. customevaporate the filtrate
  5. customPurify by silica gel chromatography
  6. washeluting with 0-6% MeOH in dichloromethane with 2 N ammonia

Sources & evidence

ORD record
ord-69042d9eeb55431099aac234f6a54de0
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

Loading…