Tetrahydro-4H-pyran-4-one → HCID 53256037, compound

HRID 1957982Notes

Reaction equation

HRID 1957982 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1>ClCCl>[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH:31]2[CH2:32][CH2:33][O:28][CH2:29][CH2:30]2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 53256037HCID 53256037, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(R)-Pyrrolidin-3-yl carbamic acid tert-butyl ester (200 mg; 1.074 mmol) was suspended in 7 ml of dichloromethane and sodium triacetoxyborohydride (455 mg; 2.15 mmol) was added. A solution of tetrahydro-4H-pyran-4-one (0.297 ml; 3.22 mmol) in 3 ml of dichloromethane was added drop-wise to the reaction mixture. The reaction mixture was maintained at room temperature overnight, it was then diluted with dichloromethane and washed with saturated sodium bicarbonate solution. The organic phase was dried with MgSO4 and concentrated in vacuo. The product was obtained after loading the crude on a SCX-cartridge and recovering with MeOH/ammonia solution. 220 mg (0.641 mmol; 60% yield) of (R)-[1-(tetrahydro-pyran-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester were obtained as colourless oil.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic phase was dried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product was obtained
  5. customrecovering with MeOH/ammonia solution

Sources & evidence

ORD record
ord-5b8e11cbf957479cacb547802f964fa4
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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