Ammonia → 5-Allyl-5-amino-cyclooctanol

HRID 2370277Notes

Reaction equation

HRID 2370277 reaction equation
[Si]([O:8][CH:9]1CCCC(=O)CC[CH2:10]1)(C(C)(C)C)(C)C.N.C(B1OC(C)(C)C(C)(C)O1)C=C.[CH2:31]([C:34]1([NH2:41])[CH2:39][CH2:38][CH:37](O)[CH2:36][CH2:35]1)[CH:32]=[CH2:33]>CO>[CH2:31]([C:34]1([NH2:41])[CH2:39][CH2:38][CH2:37][CH:9]([OH:8])[CH2:10][CH2:36][CH2:35]1)[CH:32]=[CH2:33]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 109780905-(Tert-butyldimethylsilyloxy)cyclooctanoneHCID 592260294-Allyl-4-amino-cyclohexanol

Product 1

HCID 592248295-Allyl-5-amino-cyclooctanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.89 g of 5-Allyl-5-amino-cyclooctanol (30) were synthesized as a diastereomeric mixture starting from 1.50 g (5.85 mmol) of 5-(tert-butyldimethylsilyloxy)cyclooctanone, 8.4 mL (58.5 mmol) of 7N ammonia in methanol, and 1.7 mL (9.36 mmol) of 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, following the protocol described for 4-allyl-4-amino-cyclohexanol (16). Rt=0.44 min, 0.49 min (Method C). Detected mass: 184.3 (M+H+).

Workup

  1. customRt=0.44 min, 0.49 min (Method C)

Sources & evidence

ORD record
ord-ce1e9b08c9514326b0f07fc00b5da6b4
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

Loading…