Methanol → HCID 9861827, compound

HRID 2186675Notes

Reaction equation

HRID 2186675 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([N:11]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:3][CH2:2]1.O1[CH2:22][CH2:21][CH2:20][CH2:19]1.CO.[C:25]([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:19][CH:20]([CH3:25])[CH2:21][CH2:22][N:14]1[CH2:15][CH2:16][CH2:17][N:11]([CH:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:1][CH2:2][CH2:3]2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 10198826HCID 10198826, compound

Product 1

HCID 9861827HCID 9861827, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A dry 100 ml 3-necked flask under nitrogen was charged with N-(3,4-dihydro-2H-benzothiopyran-4-yl)homopiperazine (1.0 g; 4.03 mmol) and treated sequentially with tetrahydrofuran (20 ml), methanol (10 ml), isoamyl aldehyde (5.0 ml; 46.0 mmol), sodium cyanoborohydride, (0.40 g; 6.4 mmol) and acetic acid (0.4 ml) as in Example 3. The resulting material was purified by kugelrohr distillation to give an oil (1.09 g), bp (air bath temperature) 150°-160° C. at 200 mtorr; 1H NMR (300 MHz, CD3OD) δ0.88-0.90 (d, 6H).

Workup

  1. distillationThe resulting material was purified by kugelrohr distillation

Sources & evidence

ORD record
ord-cce4069e21d44e748a74bae600349b57
Source dataset
uspto-grants-2002_06
Patent number
US06407093B1

Reaction notes

Loading…