Hydrazine hydrate (1:1) → HCID 14621518, compound

HRID 1651677Notes

Reaction equation

HRID 1651677 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][C@H:11]1[CH2:16][O:15][C@@H:14]([CH3:17])[O:13][C@H:12]1[CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O)=[O:4].O.NN>C(O)C>[NH2:19][CH2:18][C@H:12]1[C@@H:11]([CH2:10]/[CH:9]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:16][O:15][C@@H:14]([CH3:17])[O:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14621516HCID 14621516, compound

Product 1

HCID 14621518HCID 14621518, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-phthalimidomethyl-1,3-dioxane (54 mg) in ethanol (2 ml) was added hydrazine monohydrate (0.007 ml) and the mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo and the crude product was purified with preparative TLC (chloroform:methanol:conc.aqueous ammonia=85:15:0.1) to give (2R,4R,5S)-4-aminomethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (13 mg).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude product was purified with preparative TLC (chloroform:methanol:conc.aqueous ammonia=85:15:0.1)

Sources & evidence

ORD record
ord-04963cc61a5644b2b6db67e8963c120f
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

Loading…