Water → HCID 13911561, compound

HRID 653391Notes

Reaction equation

HRID 653391 reaction equation
[Si]([O:8][CH:9]1[C:16](=[O:17])[N:15]2[CH:11]([CH2:12][CH2:13][C:14]2=[O:18])[CH2:10]1)(C(C)(C)C)(C)C.O>C(O)(=O)C>[OH:8][CH:9]1[C:16](=[O:17])[N:15]2[CH:11]([CH2:12][CH2:13][C:14]2=[O:18])[CH2:10]1

Participants

4

Reactant 2

HCID 962WaterHCID 13911565HCID 13911565, compound

Product 1

HCID 13911561HCID 13911561, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-t-butyldimethylsilyloxy-dihydro-1H-pyrrolizine-3,5(2H,6H)-dione (2.1 g) in acetic acid:water, 3:1 (18 ml) is stirred at 60° C. for six hours. The solution is cooled, concentrated, toluene added and the solution reconcentrated. The oil is triturated with anhydrous ethyl ether and filtered to yield 2-hydroxy-dihydro-1H-pyrrolizine-3,5(2H,6H)-dione as a white solid with mp 135°-140° C. NMR (CDCl3) and 5.48 (m, 1H), 4.47 (m, 1H), 4.10 (b.s., 1H), 2.93-1.36 (m, 6H). IR 3310, 2860, 1770, 1710, 1655, 1410, 1372, 1307, 1275.

Workup

  1. temperatureThe solution is cooled
  2. concentrationconcentrated
  3. additiontoluene added
  4. customThe oil is triturated with anhydrous ethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3c1432741b3946a8a85528136c1e6862
Source dataset
uspto-grants-1987_06
Patent number
US04677098

Reaction notes

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