1,3-Propanediol → HCID 58313061, compound

HRID 454419Notes

Reaction equation

HRID 454419 reaction equation
[O:1]=[C:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:17]([O:19][CH3:20])=[O:18])[CH2:3]1.[CH2:21](O)[CH2:22][CH2:23][OH:24].C[C@H]1C[C@H](C)OC2(CN(C(=O)[C@H](C(C)C)NC(OC)=O)[C@H](C(OC)=O)C2)O1>>[CH2:6]1[C:2]2([O:24][CH2:23][CH2:22][CH2:21][O:1]2)[CH2:3][C@@H:4]([C:17]([O:19][CH3:20])=[O:18])[N:5]1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

4

Reactant 3

HCID 104421,3-PropanediolHCID 115942881-Benzyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateHCID 58313150HCID 58313150, compound

Product 1

HCID 58313061HCID 58313061, compoundYield 84.3%

Procedure

3-Methyl 2-(phenylmethyl) (3S)-6,10-dioxa-2-azaspiro[4.5]decane-2,3-dicarboxylate (Intermediate 24) (1.02 g, yield 84%) was prepared from 2-methyl 1-(phenylmethyl) (2S)-4-oxo-1,2-pyrrolidinedicarboxylate (1.0 g, 3.61 mmol) and 1,3-propanediol (0.55 g, 7.21 mmol) following the similar procedure outlined in the preparation of Intermediate 14 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.05-7.61 (m, 5H) 4.91-5.25 (m, 2H) 4.29-4.68 (m, 1H) 3.75-4.07 (m, 5H) 3.38-3.75 (m, 4H) 2.25-2.67 (m, 2H) 1.51-2.00 (m, 1H). ES LC-MS m/z=336.6 (M+H)+.

Sources & evidence

ORD record
ord-0ee24e80e9114507b229e1f6c11d458c
Source dataset
uspto-grants-2013_07
Patent number
US08492554B2

Reaction notes

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