Borane → HCID 22628911, compound

HRID 277341Notes

Reaction equation

HRID 277341 reaction equation
[CH2:1]([CH:8]1[C:31](=O)[N:30]([CH3:33])[CH:29]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:28](=[O:38])[O:27][CH:26]([CH3:39])[CH2:25][N:24]([CH3:40])[CH:23]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:22](=[O:45])[O:21][CH:20]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:19](=O)[N:18]([CH3:54])[CH:17]([CH2:55][CH:56]([CH3:58])[CH3:57])[C:16](=[O:59])[O:15][CH:14]([CH3:60])[CH2:13][N:12]([CH3:61])[CH:11]([CH2:62][CH:63]([CH3:65])[CH3:64])[C:10](=[O:66])[O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1CCCCC1.C(OCC)(=O)C>C1COCC1>[CH2:46]([CH:20]1[CH2:19][N:18]([CH3:54])[CH:17]([CH2:55][CH:56]([CH3:58])[CH3:57])[C:16](=[O:59])[O:15][CH:14]([CH3:60])[CH2:13][N:12]([CH3:61])[CH:11]([CH2:62][CH:63]([CH3:65])[CH3:64])[C:10](=[O:66])[O:9][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:31][N:30]([CH3:33])[CH:29]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:28](=[O:38])[O:27][CH:26]([CH3:39])[CH2:25][N:24]([CH3:40])[CH:23]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:22](=[O:45])[O:21]1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

5

Reactant 3

HCID 6331BoraneHCID 21867204Cyclohexane ethylacetateHCID 22628884HCID 22628884, compound

Product 1

HCID 22628911HCID 22628911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the method of Example 1, 2.99 g (3.25 mmol) of 8,20-dibenzyl-5,11,17,23-tetraisobutyl-2,4,10,14,16,22-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-6,9,12,18,21,24-hexaone (1-b) (for example from Ex. 1) in 20 ml of THF were reacted with 9.75 ml (9.75 mmol) of a 1M solution of borane. Column chromatography (silica gel, Ø=4.5 cm, l=25 cm; cyclohexane:ethyl acetate 50:1 to 5:1) gave 0.72 g of tetrareduction product 8,20-dibenzyl-5,11,17,23-tetraisobutyl-2,4,10,14,16,22-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-6,12,18,24-tetraon (2) (cf. Ex. 2), 0.22 g of trireduction product (1-c) and 0.91 g of unreacted starting material.

Sources & evidence

ORD record
ord-13bdf77abf2e476bbfa624dee9990bd0
Source dataset
uspto-grants-2002_03
Patent number
US06355615B1

Reaction notes

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