Hydrochloric Acid → HCID 67373194, compound

HRID 1517547Notes

Reaction equation

HRID 1517547 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:34]([O:41][CH3:42])=[CH:33][C:16]=2[CH2:17][N:18]2[C@H:22]([C:23](C)(C)[O:24][SiH2]C(C)(C)C)[CH2:21][CH2:20][C:19]2=[O:32])=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:36]=[C:35]([C:37]([CH3:38])([CH3:40])[CH3:39])[C:34]([O:41][CH3:42])=[CH:33][C:16]=2[CH2:17][N:18]2[C@H:22]([CH2:23][OH:24])[CH2:21][CH2:20][C:19]2=[O:32])=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131729854HCID 131729854, compound

Product 1

HCID 67373194HCID 67373194, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

step 3—To a solution of 106 (128 mg, 0.22 mmol) and THF (10 mL) under an argon atmosphere was added dropwise (n-Bu)4N+F− (0.24 mL, 1M in THF). After 1 h the mixture was poured into 1N HCl, extracted with EtOAc, washed with brine, dried (MgSO4), filtered and concentrated to afford 100 mg (97%) of (S)-1-[2-(2-benzyloxy-pyridin-3-yl)-4-tert-butyl-5-methoxy-benzyl]-5-hydroxymethyl-pyrrolidin-2-one (108).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2deb82a1e4a74bcea85ef37081078025
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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