Acetic Acid → tert-Butyl N-[(3S)-1-(cyclohex-1-en-1-ylmethyl)pyrrolidin-3-yl]carbamate

HRID 446023Notes

Reaction equation

HRID 446023 reaction equation
[C:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:9]([O:13][C:14]([NH:16][C@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[C:1]1([CH2:7][N:19]2[CH2:20][CH2:21][C@H:17]([NH:16][C:14](=[O:15])[O:13][C:9]([CH3:11])([CH3:10])[CH3:12])[CH2:18]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 51845401-Cyclohexene-1-carboxaldehyde

Product 1

HCID 71293742tert-Butyl N-[(3S)-1-(cyclohex-1-en-1-ylmethyl)pyrrolidin-3-yl]carbamateYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Cyclohexene-1-carboxaldehyde (1.48 ml, 13 mmol) was added to a mixture of (3S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine (2.0 g, 10.8 mmol), acetic acid (1.24 ml, 21.6 mmol) and tetrahydrofuran (dehydrated) (27 ml), followed by stirring at mom temperature for 15 minutes, and sodium triacetoxyborohydride (4.58 g, 21.6 mmol) was then added and the reaction mixture was stirred at mom temperature for 17 hours and 45 minutes. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was distilled off. The residue was purified by NH silica gel column chromatography (elution solvent: ethyl acetate/heptane) to give the title compound (1.3 g, yield: 42.9%).

Workup

  1. stirringthe reaction mixture was stirred at mom temperature for 17 hours and 45 minutes
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by NH silica gel column chromatography (elution solvent: ethyl acetate/heptane)

Sources & evidence

ORD record
ord-3728b9411c2d4e8c988fd829be3e72bd
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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