(R)-tert-Butyl 2-((R)-(4-(benzyloxy)phenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylate → (R)-tert-butyl 2-((R)-(4-hydroxyphenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylate

HRID 1874649Notes

Reaction equation

HRID 1874649 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:28][C:29](=[O:38])[C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:31])[C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:28][C:29](=[O:38])[C@H:30]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH3:31])[C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 86658402(R)-tert-Butyl 2-((R)-(4-(benzyloxy)phenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67438445(R)-tert-butyl 2-((R)-(4-hydroxyphenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-tert-Butyl 2-((R)-(4-(benzyloxy)phenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylate (78 mg, 0.152 mmol) and palladium on carbon (10% wt) (36 mg, 0.034 mmol) in methanol (3.031 mL) was hydrogenated under 60 psi hydrogen gas for 4 h. The mixture was filtered through diatomaceous earth (Celite®) eluting with EtOAc and the filtrate concentrated in vacuo. Obtained (R)-tert-butyl 2-((R)-(4-hydroxyphenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylate (29.1 mg, 0.069 mmol, 98% yield) as a colorless oil which was carried forward without further purification. 1H NMR (400 MHz, CDCl3) δ 8.17 (d, J=5.79 Hz, 1H), 7.25-7.31 (m, 1H), 7.13-7.23 (m, 4H), 6.91 (d, J=8.31 Hz, 2H), 6.52 (d, J=8.56 Hz, 2H), 4.45 (dd, J=10.83, 6.04 Hz, 1H), 3.99-4.14 (m, 1H), 3.27-3.57 (m, 3H), 1.72-2.07 (m, 2H), 1.59 (t, J=11.46 Hz, 2H), 1.51 (s, 9H), 1.42 (d, J=7.30 Hz, 3H); LRMS (ESI) m/e 447.20 [(M+Na)+, calcd for C25H32N2NaO4 447.23].

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth (Celite®)
  2. washeluting with EtOAc
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-0c7da4c9b42e4dae9c57ff6ac0d26112
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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