Aluminium lithium hydride → HCID 71574550, compound

HRID 2369342Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH2:12][C:13]3[N:17]([CH2:18][C:4]1=2)[C:16]([CH3:19])=[C:15]([C:20](OC)=[O:21])[C:14]=3[C:24](OC)=[O:25])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH2:12][C:13]3[N:17]([CH2:18][C:4]1=2)[C:16]([CH3:19])=[C:15]([CH2:20][OH:21])[C:14]=3[CH2:24][OH:25])[CH3:2]

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 71574639HCID 71574639, compound

Product 1

HCID 71574550HCID 71574550, compound

Procedure

Compound BO-1972 was prepared from dimethyl 6-ethyl-3-methyl-6,11-dihydro-5H-indolizino-[6,7-b]indole-1,2-dicarboxylate (3.6 g, 10 mmol) and LiAlH4 (0.92 g, 25 mmol). Yield 2.5 g (80%); mp 216-217° C. 1H NMR (DMSO-d6) δ 1.29 (3H, t, J=7.1 Hz, Me), 2.30 (3H, s, Me), 4.00 (2H, s, CH2), 4.21 (2H, q, J=7.1 Hz, CH2), 4.38 (3H, br s, CH2 and exchangeable, OH), 4.44 (3H, br s, CH2 and exchangeable, OH), 5.13 (2H, s, CH2), 7.04-7.07 (1H, m, ArH), 7.14-7.18 (1H, m, ArH), 7.47-7.49 (1H, m, ArH), 7.53-7.55 (1H, m, ArH). Anal. Calcd for (C19H22N2O2): C, 73.52; H, 7.14; N, 9.03. Found: C, 73.68; H, 6.93; N, 8.66.

Sources & evidence

ORD record: ord-36113f6d21294cf4ae704665120b9193
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703951B2

Reaction notes

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