HCID 178454077, compound → HCID 178454079, compound

HRID 1912721Notes

Reaction equation

HRID 1912721 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][CH2:14]1>CO.NN>[C:22]([O:21][C:20]([NH:19][C@@H:16]1[CH2:15][CH2:14][C@H:13]([O:12][NH2:3])[CH2:18][CH2:17]1)=[O:26])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 178454077HCID 178454077, compound

Product 1

HCID 178454079HCID 178454079, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9321HydrazineSolvent

Procedure

A suspension of tert-butyl cis-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]-cyclohexylcarbamate (2.00 g) in MeOH (23 mL), hydrazine (26% in water, 1.1 mL) was added. After stirring at room temperature for 30 min, the mixture was filtered. The filtrate was evaporated to dryness and purified by flash chromatography (SiO2, CH2Cl2:MeOH 9:1) to give cis-4-(tert-butoxycarbonyl)aminocyclohexyloxyamine (0.80 g, 63%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 6.73 (1H, d), 5.75 (2H, bb), 3.45 (1H, m), 3.21 (1H, m), 1.30-1.90 (8H, m), 1.36 (9H, s).

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness
  4. custompurified by flash chromatography (SiO2, CH2Cl2:MeOH 9:1)

Sources & evidence

ORD record
ord-57b755d7e9834747883957e2be1e62e4
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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