Aminoacetaldehyde dimethyl acetal → Phenylmethyl 2-(2,2-dimethoxyethyl)hydrazinecarboxylate

HRID 1737847Notes

Reaction equation

HRID 1737847 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[C:8]([N:18]1C(C2C=CC=CC=2)O1)([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]>C(Cl)Cl>[C:8]([NH:18][NH:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 11118644HCID 11118644, compound

Product 1

HCID 21843455Phenylmethyl 2-(2,2-dimethoxyethyl)hydrazinecarboxylateYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Aminoacetaldehyde dimethyl acetal (0.430 g, 3.95 mmol) was added to a solution of N-CBZ-3-phenyl-oxaziridine (1.11 g, 4.35 mmol) (prepared as described in Tetrahedron Let. 1993, 6859, the disclosure of which is entirely incorporated herein by reference) in CH2Cl2 (20 mL) at 23° C. The resulting yellow solution was stirred at 23° C. for 18 h, and it then was concentrated under reduced pressure. Purification of the residue by flash column chromatography (3% CH3OH/CH2Cl2) provided 1-CBZ-2-(2,2-dimethoxyethyl)-hydrazine (0.434 g, 43%) as a pale yellow oil: Rf =0.40 (5% CH3OH/CH2Cl2); IR (thin film) 3317, 1721, 1456 cm-1 ; 1H NMR (C6D6) δ 2.96 (bs, 2H), 3.06 (bs, 6H), 3.97 (bs, 1H), 4.37 (bs, 1H), 4.97 (bs, 2H), 5.87 (bs, 1H), 6.98-7.18 (m, 5H).

Workup

  1. customprepared
  2. customat 23° C
  3. concentrationit then was concentrated under reduced pressure
  4. customPurification of the residue by flash column chromatography (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ffd49aaefd8242f7b50f15786c5964e2
Source dataset
uspto-grants-1999_10
Patent number
US05962487

Reaction notes

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