Ethanol → HCID 18661289, compound

HRID 965237Notes

Reaction equation

HRID 965237 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:39]=[CH:38][C:18]([O:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][C@@H:21]2[N:29]([CH3:37])[C:30](OC(C)(C)C)=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O1CCCC1.C(O)C.C(Cl)(Cl)[Cl:49]>>[ClH:49].[CH2:7]([O:14][C:15]1[CH:39]=[CH:38][C:18]([O:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][C@@H:21]2[N:29]([CH3:37])[CH3:30])=[CH:17][CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6212ChloroformHCID 8028TetrahydrofuranHCID 18661291cis-1-(4-benzyloxyphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18661289HCID 18661289, compound

Procedure

The title compound was prepared in a similar manner to Example 12 from LiAlH4 (769 mg, 20.2 mmol), cis-1-(4-benzyloxyphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indane (900 mg, 2.02 mmol) and tetrahydrofuran (50 ml). After a reaction time of 3 hours the reaction was worked up as previously described and subjected to column chromatography on silica gel eluting with 5% ethanol in chloroform to afford a pale green oil (640 mg) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. 215°-216° C. dec. (from methanol-diethyl ether).

Workup

  1. customAfter a reaction time of 3 hours

Sources & evidence

ORD record
ord-d239f0b1f9ab43cbbe4b283efc7049ca
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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