Triphenylphosphine → HCID 19017868, compound

HRID 1728361Notes

Reaction equation

HRID 1728361 reaction equation
[CH:1]1([CH2:8]O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC([O:17][NH:18][C:19](=[O:25])OC(C)(C)C)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/[N:50]=N/C(OCC)=O)=O>C1COCC1>[OH:17][N:18]([CH2:8][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)[C:19]([NH2:50])=[O:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 78193CycloheptanemethanolHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 19017868HCID 19017868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of cycloheptanemethanol (11.2 g, 100 mmol), tert-butyl N-(tert-butoxycarbonyloxy)carbamate (7.2 g, 104 mmol) and triphenylphosphine (7.2 g, 104 mmol) in THF (150 mL) was added diethylazodicarboxylate dropwise. The mildly exothermic reaction was stirred 3 hours, then concentrated in vacuo. The concentrate was treated with hexane, and the crystalline by-product was vacuum filtered. The filtrate was concentrated in vacuo and the resulting residue was chromatographed (silica gel, ethyl acetate:hexanes, 2:8) to afford the protected hydroxylamine derivative.

Workup

  1. customThe mildly exothermic reaction
  2. concentrationconcentrated in vacuo
  3. additionThe concentrate was treated with hexane
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting residue was chromatographed (silica gel, ethyl acetate:hexanes, 2:8)

Sources & evidence

ORD record
ord-b67b7708f66d424fb90b6bf6a29cfb12
Source dataset
uspto-grants-1994_07
Patent number
US05326787

Reaction notes

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