Acetic Acid → HCID 86613443, compound

HRID 630360Notes

Reaction equation

HRID 630360 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][NH:14][CH2:15][CH:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:30](O)(=O)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH3:30][N:14]([CH2:15][C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:29][CH:28]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68489504HCID 68489504, compound

Product 1

HCID 86613443HCID 86613443, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 2-[[[[4-(4-bromophenoxy)phenyl]methyl]amino]-methyl]-1-pyrrolidinecarboxylate (900 mg, 1.9 mmol) in dichloroethane (10 mL) was stirred as acetic acid (180 mg, 3 mmol), formaldehyde (37% solution in water) and sodium triacetoxyborohydride (508 mg, 2.4 mmol) were added. The reaction was stirred for 17 hours. The reaction was treated with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (2×). The combined organic extracts were dried and concentrated. Purification by flash chromatography on silica gel using a mixture of ethyl acetate in hexane gave 0.67 g of 1,1-dimethylethyl (R)-2-[[methyl[[4-(4-bromophenoxy)phenyl]methyl]amino]methyl]-1-pyrrolidinecarboxylate.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate (2×)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel using
  6. additiona mixture of ethyl acetate in hexane

Sources & evidence

ORD record
ord-057daf56ce1b488ab76e34f747eeb252
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

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