tert-Butanol → HCID 178426226, compound

HRID 1044373Notes

Reaction equation

HRID 1044373 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@:10]3([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[Cl:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=1I.C(=O)([O-])[O-].[K+].[K+].[C@H]1(O)CCCC[C@@H]1O.C(O)(C)(C)C>[Cu]I>[Cl:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=1[N:14]1[CH2:15][CH2:16][CH2:17][C@@:10]2([C:9](=[O:18])[N:8]([C@H:5]3[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]3)[CH2:12][CH2:11]2)[CH2:13]1

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 11430Potassium CarbonateHCID 27576182-Chloro-1-iodo-4-methylbenzeneHCID 70571101,2-Cyclohexanediol, (1S-trans)-HCID 178517864HCID 178517864, compound

Product 1

HCID 178426226HCID 178426226, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

A mixture of (5S)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (20 mg, 0.00007 mol) which was prepared using procedures analogous to those described in the synthesis of example 472-a and followed by standard hydrogenation to remove the carbobenzyloxy (Cbz) protecting group and 2-chloro-1-iodo-4-methylbenzene (22.7 mg, 0.0000831 mol), potassium carbonate (20.1 mg, 0.000145 mol), copper(I) iodide (0.6 mg, 0.000003 mol), and (1S,2S)-cyclohexane-1,2-diol (16.1 mg, 0.000138 mol) in tert-butyl alcohol (1.0 mL, 0.010 mol) was heated at 100° C. for 18 h. The crude product was purified by prep-HPLC to afford the desired product. LC-MS: 377.1 (M+H)+.

Workup

  1. customwas prepared
  2. customthose described in the synthesis of example 472-a
  3. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-51664176d7554bc2a46926772c8334ea
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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