HCID 13966776, compound → HCID 21866184, compound

HRID 857759Notes

Reaction equation

HRID 857759 reaction equation
C([O:3][C:4]([C:6]1(C(OCC)=O)[CH:10]([CH:11]([CH3:13])[CH3:12])[CH2:9][CH2:8][NH:7]1)=[O:5])C.C(C1CCNC1C(O)=O)C.C(C1(C(OCC)=O)C(CC)CCN1)(OCC)=O>>[CH:11]([CH:10]1[CH2:9][CH2:8][NH:7][CH:6]1[C:4]([OH:5])=[O:3])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 13966776HCID 13966776, compoundHCID 13966777HCID 13966777, compoundHCID 21866311HCID 21866311, compound

Product 1

HCID 21866184HCID 21866184, compound

Procedure

The title compound was prepared from diethyl-3-isopropylpyrrolidine-2,2-dicarboxylate (3.06 g, 12.0 mmol) essentially according to the basic hydrolysis procedure described in Morgan, B. A.; Schafer, D. J. U.S. Pat. No. 4,060,603, Nov. 29, 1977 for the preparation of 3-ethyl-dl-proline from 2,2-dicarboethoxy-3-ethylpyrrolidine. The product was isolated as a yellow solid. LCMS (M+H): 158.0. 1H NMR (CD3OD, 400 MHz): δ 3.70 (d, J=6.4 Hz, 1 H), 3.31–3.27 (m, 1 H), 2.29–2.22 (m, 1 H), 2.08–1.99 (m, 1 H), 1.94–1.74 (m, 3 H), 1.05 (d, J=6.8 Hz), 0.97(d, J=6.8Hz, 3 H).

Workup

  1. customessentially according to the basic hydrolysis procedure
  2. customThe product was isolated as a yellow solid

Sources & evidence

ORD record
ord-8b201d8b2c6e47a59d233434e47c001e
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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