Acetic Acid → HCID 67315625, compound

HRID 1011880Notes

Reaction equation

HRID 1011880 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[C:21](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.C([BH3-])#N.[Na+]>C(Cl)Cl.CCO>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]([CH3:21])[CH:17]2[CH2:18][CH2:19][O:14][CH2:15][CH2:16]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 712FormaldehydeHCID 121599Tetrahydro-4H-pyran-4-oneHCID 1519354(3R)-1-benzylpyrrolidin-3-amineHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67315625HCID 67315625, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-benzyl-pyrrolidin-3-ylamine (1.0 g, 6 mmol), tetrahydro-4H-pyran-4-one (0.6 g, 6 mmol) in CH2Cl2 (15 ml) was added acetic acid (0.7 ml, 11 mmol) and sodium triacetoxyborohydride (1.4 g, 7 mmol) and the reaction stirred for 1 h. EtOH (15 ml) was added to the reaction, followed by formaldehyde (1 ml, 36% solution in water) and finally sodium cyanoborohydride (0.4 g, 7 mmol) and the reaction stirred for a further 15 minutes. The reaction was then concentrated, the residue redissolved in CH2Cl2, washed with saturated NaHCO3, dried (Na2SO4) and concentrated. Purification by flash column chromatography (CH2Cl2:MeOH 9:1) afforded the title product (0.7 g, 44%) as a brown oil. MS: 275.2 (MH+).

Workup

  1. stirringthe reaction stirred for a further 15 minutes
  2. concentrationThe reaction was then concentrated
  3. dissolutionthe residue redissolved in CH2Cl2
  4. washwashed with saturated NaHCO3
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (CH2Cl2:MeOH 9:1)

Sources & evidence

ORD record
ord-06b99aff6a5344bd82d3c7566e30be54
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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