1-Isocyanatoadamantane → 6-(Adamantan-1-ylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester

HRID 2407541Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:11]2([CH2:14][NH:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:15]([C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[C:16]=[O:17]>>[C:1]([O:5][C:6]([N:8]1[C:11]2([CH2:12][N:13]([C:16](=[O:17])[NH:15][C:18]34[CH2:19][CH:20]5[CH2:26][CH:24]([CH2:23][CH:22]([CH2:21]5)[CH2:27]3)[CH2:25]4)[CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 20599951-Isocyanatoadamantane

HCID 56828076Tert-butyl 1,6-diazaspiro[3.3]heptane-1-carboxylate

Product 1

HCID 866823526-(Adamantan-1-ylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester

Procedure

In analogy to the experimental procedure of example 8) 1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester instead of 1-benzyl-1,6-diaza-spiro[3.3]heptane was converted using 1-isocyanato-adamantane instead of (3-isocyanato-propyl)-benzene into the title compound which was used directly in the next step without further purification.

Sources & evidence

ORD record: ord-4a3a7eb0c450419e9c214d82471352c1
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809552B2

Reaction notes

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