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Acetic Acid → (R)-3-(2,6-dichloro-4-hydroxy-benzyl)-1-(tetrahydro-pyran-4-yl)-pyrrolidin-2-one

HRID 415991
Notes
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Reaction equation

HRID 415991 reaction equation
[CH2:1]([C@@H:8]1[CH2:12]OC(=O)[N:9]1[C:14](=[O:36])[CH:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27]CC2C=CC=CC=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=O)[C:2]1C=CC=CC=1.NC1CC[O:41][CH2:40]C1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:26][C:25]1[CH:24]=[C:23]([OH:27])[CH:22]=[C:21]([Cl:35])[C:20]=1[CH2:19][C@@H:15]1[CH2:16][CH2:17][N:9]([CH:8]2[CH2:1][CH2:2][O:41][CH2:40][CH2:12]2)[C:14]1=[O:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4192234-AminotetrahydropyranHCID 5049666Sodium triacetoxyborohydrideHCID 866312304-(4-(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

Product 1

HCID 66621933(R)-3-(2,6-dichloro-4-hydroxy-benzyl)-1-(tetrahydro-pyran-4-yl)-pyrrolidin-2-oneYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of 4-(4-(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde (Preparation 27) (10.4 g, 20 mmol) and 4-aminotetrahydropyran (2 g, 20 mmol) in dichloromethane (100 mL) with acetic acid (1 mL, 20 mmol). Stir the reaction 1 hr at room temperature then add sodium triacetoxyborohydride (12.6 g, 60 mmol) and stir for an additional 4 hr at room temperature. Quench with water and separate the organic layer. Wash with brine, dry over magnesium sulfate, filter, and remove the solvent under vacuum. Purify by silica gel column chromatography using hexanes:ethyl acetate to afford 4.93 g (57%) of desired product: MS (m/z): 434 (M+).

Workup

  1. customthe reaction 1 hr at room temperature
  2. customQuench with water
  3. customseparate the organic layer
  4. washWash with brine
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. customremove the solvent under vacuum
  8. customPurify by silica gel column chromatography

Sources & evidence

ORD record
ord-6b682c43ac284519884c4c9579ea6173
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088776B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes